Degradable monomer based on cyclic acetal structure as well as synthesis method and application of degradable monomer

A cyclic acetal and synthesis method technology, applied in recycling technology, organic chemistry, plastic recycling, etc., can solve the problems of large resin shrinkage rate and high curing temperature, and achieve good controllability, simple synthesis process, and excellent mechanical properties Effect

Active Publication Date: 2021-06-08
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, during the curing process of these materials, small molecules of water will be removed, and solvents with

Method used

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  • Degradable monomer based on cyclic acetal structure as well as synthesis method and application of degradable monomer
  • Degradable monomer based on cyclic acetal structure as well as synthesis method and application of degradable monomer
  • Degradable monomer based on cyclic acetal structure as well as synthesis method and application of degradable monomer

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Example Embodiment

[0033] Another aspect of the embodiment of the present invention provides a synthetic method of a degradable monomer based on a cyclic acetal structure comprising: a hydroxybenzaldehyde substance comprising: a catalyst presence or uncovatively catalyst. The mixture of glycerol was reacted at 10 to 180 ° C to obtain a degradable monomer based on a cyclic acetal structure.

[0034] In some embodiments, the hydroxybenzaldehyde substance has the structure shown in the formula:

[0035]

[0036] R 1 R 2 R 3 R 4 R 5 At least one of the medium is a hydroxyl group, at least the other independently selected from the substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy or hydroxyl group, and the remaining selected from H, substituted or unsubstituted alkyl, substituted or Unsubstituted alkoxy or hydroxyl groups.

[0037] In some embodiments, the molar ratio of the glycerol and the hydroxybenzallade is 1: 1 to 10.

[0038] In some embodiments, the catalyst comprises any ...

Example Embodiment

[0068] Example 1

[0069] (1) Take 15.2 g of vanillic aldehyde, 10 g of glycerol and 0.15 g of phosphoric acid, no additional solvent, at 110 ° C for 6 h, to the solid precipitation reaction. Using a small amount of water, acetone washing, filtration, drying, and obtained the final product. The structural formula is as shown in the following formula I-1, and the yield is 90%. 1 H-NMR, such as figure 1 As shown, the hydrogen above the respective peaks on the figure is one or one.

[0070]

[0071] (2) 10 g of the compound, 0.1 g of tetrabutylammonium bromide, 25 g 50 wt% of aqueous potassium hydroxide, and 50 ° C in a solution of 5 h. Subsequently, 50 g of epoxy chloropropane was added dropwise to 10 ° C or less, and 50 g of epoxy chloropropane was added dropwise, and 0.5 h was added. After the drop is added, the reaction is at room temperature for 48 h. Subsequently, 30 mL of dichloromethane was added, washed 3 times with deionized water, and the organic phase was retained. Emme...

Example Embodiment

[0073] Example 2

[0074] (1) 15.2 g of 2,4-dihydroxy-3-methylbenzaldehyde, 10 g of glycerol and 0.15 g of citric acid mix, add 30 mln, N-dimethylformamide and 40 ml of petroleum ether, reacted at 100 ° C for 12h No more water in the divided water is separated, and the reaction is completed. The upper petroleum ether was then removed, washed with a small amount of water, acetone, and dried filtration, and dried to obtain the final product. Nuclear magnetic resonance 1 H-NMR and infrared characterization determine that the final product formula is shown in Formula I-2, and the yield is 80%.

[0075]

[0076] (2) 10 g of Tetrabutyla bromine, 500 g of tetrabutylammonium bromide, 500 g of tetrabutylammonium bromide, and 500 g of tetrabutylammonium bromide, and 500 g of 500 g of aqueous potassium hydroxide. Subsequently to -5 ° C, 500 g of epoxy chloropropane was added dropwise through the constant pressure divider, and 5 h was added. After the drop is added, the room temperature rea...

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Abstract

The invention discloses a degradable monomer based on an acetal structure and a synthesis method of the degradable monomer. The degradable monomer has a structure as shown in a formula I which is described in the specification. In the formula I, at least one of R<1>, R<2>, R<3>, R<4> and R<5> is a hydroxyl group, at least another one of R<1>, R<2>, R<3>, R<4> and R<5> is independently selected from substituted or unsubstituted alkyl group and a substituted or unsubstituted alkoxy or hydroxyl group, and the rest are selected from H, the substituted or unsubstituted alkyl group and the substituted or unsubstituted alkoxy or hydroxyl group. The invention also discloses a method for synthesizing epoxy resin by using the degradable monomer and the epoxy resin obtained by using the method. When the degradable monomer provided by the invention is used for synthesizing various materials such as the epoxy resin, the materials can be endowed with good degradability, excellent mechanical properties, excellent heat resistance and relatively high glass transition temperature; and the synthesis method is simple in process, easy and convenient to operate, good in controllability, easy to implement and suitable for large-scale industrial production; and wide application prospects are obtained in the fields of coatings, fiber composite materials, aerospace and the like.

Description

technical field [0001] The invention relates to a compound that can be used to prepare epoxy resin, in particular to a degradable monomer based on a cyclic acetal structure, its synthesis method and its application in epoxy resin, belonging to the technical field of polymer materials . Background technique [0002] Plastic plays a vital role in contemporary society. Due to its excellent performance, plastics have been widely used in furniture, daily necessities, medical care, agriculture, fishery, transportation, construction industry, chemical industry, aerospace and many other fields, driving the development of society and the progress of human civilization. However, the difficult problem of subsequent processing makes traditional plastics face severe challenges. The traditional incineration and landfill methods of waste plastics have serious defects, such as the greenhouse gas or toxic substances produced by the former and the waste and pollution of land resources by th...

Claims

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Application Information

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IPC IPC(8): C07D319/06C07D407/14C08G59/04
CPCC07D319/06C07D407/14C08G59/04Y02W30/62
Inventor 马松琪王滨搏朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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